CN107205384A - Synergistic antimicrobial compositions - Google Patents
Synergistic antimicrobial compositions Download PDFInfo
- Publication number
- CN107205384A CN107205384A CN201680008326.6A CN201680008326A CN107205384A CN 107205384 A CN107205384 A CN 107205384A CN 201680008326 A CN201680008326 A CN 201680008326A CN 107205384 A CN107205384 A CN 107205384A
- Authority
- CN
- China
- Prior art keywords
- aqueous medium
- diamines
- antimicrobial compositions
- microorganism
- synergistic antimicrobial
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2303/00—Specific treatment goals
- C02F2303/20—Prevention of biofouling
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The present invention relates to a kind of Synergistic antimicrobial compositions, it is included：(a) diamines and the double benzyl acid amides of (b) disulfide group 2,2'.
Description
The present invention relates to biocide combinations, the activity of the combination is more than what is observed in single Antimicrobe compound
Activity.
Potential market, reduction concentration and cost can be widened using the combination of at least two Antimicrobe compounds,
And reduce waste.In some cases, under high concentration, commercially available Antimicrobe compound can not be also provided to micro-
Biological effective control, because its activity for resisting certain form of microorganism is weaker or relatively slow antimicrobial
Activity, or such as high temperature and high ph-values it is some under the conditions of unstability.The combination of different Antimicrobe compounds is used sometimes
Controlled or in specific final use environment with the micro- of relatively low usage rate offer phase same level in providing the entirety to microorganism
BIOLOGICAL CONTROL.Moreover, it has been discovered that synergy is a kind of uncertain phenomenon.Generally, it is similar when being combined with concrete activity
Compound show different collaboration overviews.It can happen that being not show synergy or sent out in the range of different collaborations
Raw synergy.Because this observation as a result, it is difficult to (if not impossible to) collaboration overview based on a class compound summarizes
Go out a kind of conclusion of the collaboration overview on compound.Therefore, it is necessary to find more synergistic combinations and its collaboration scope.
A kind of this kind of example of synergy is found in United States Patent (USP) case the 5,385,896th.This bibliography is public
The combination of phosphonium salt and aldehyde is opened, but this bibliography does not propose any combination claimed herein.Still need that there is enhancing
Active Antimicrobe compound other effective controls being combined to provide to microorganism.The problem of present invention is solved is to carry
For the combination of this kind of Antimicrobe compound.
The content of the invention
The present invention relates to Synergistic antimicrobial compositions, it is included：(a) diamines；Disulfide group -2,2'- pair-benzene first (b)
Base acid amides；The weight ratio of wherein -2,2'- pairs-benzyl acid amides of diamines and disulfide group is 10:1 to 1:10.
Embodiment
As used herein, unless the context clearly, otherwise following term has specified definition.Term
" Antimicrobe compound " is the growth or propagation that refer to suppress microorganism and/or the compound for killing microorganism；Resist micro- life
Compounds include bactericide, bactericide, bacteriostatic agent, ablastins, fungicide, fungistat, algicide and algae-inhibiting agent,
Depending on institute's applied dose level, system condition and required control of microorganisms degree.Term " microorganism " is included for example
Fungi (such as yeast and mould), bacterium and algae.This specification uses following abbreviation in the whole text：Ppm=by weight million
Divide rate (w/w), mL=milliliters.Unless otherwise indicated, otherwise temperature with degree Celsius (DEG C) for unit, and hundred mentioned
It is by weight (weight %) to divide ratio.The percentage of Antimicrobe compound is with active in composition in the composition of the present invention
The gross weight meter of composition, i.e. by Antimicrobe compound in itself in terms of, solvent, supporting agent not including any amount that may be present, point
Powder, stabilizer or other materials.Finally, comprising all value range end points and be combined (to be such as expressed as 10:1 arrives
1:10 or 3:1 and 1:3 scope can also include such as 10:3).
As used herein, diamines refers to N- (3- aminopropyls)-N- dodecyls propyl- 1,3- diamines, catalog number (Cat.No.)
2372-82-9, and disulfide group -2,2'- pair-benzyl acid amides or " DTBMA " correspond to catalog number (Cat.No.)：2527-58-4.
In some embodiments of the invention, the weight ratio of diamines and disulfide group -2,2'- pair-benzyl acid amides (DTBMA)
It is 10:1 to 1:10, or 9:1 to 1:9, or 3:1 to 1:3.
In some embodiments of the invention, antimicrobial combination is applied to suppress the microorganism growth of aqueous medium,
For example as in-can preservation agent.Composition applies also for controlling the microorganism of other aqueous mediums, including but not limited to work
Industry water and the contaminated culture medium of water-bearing media/water, such as cooling water, air washer, heat exchanger, boiler water, paper pulp and make
Paper plant's water, other industrial process aqueous mediums, such as：It is ballast water, waste water, metal working fluids, oil gas, latex, paint, coating, viscous
Mixture, ink, band bond compound, pigment, the slurry based on water, personal nursing and household products, such as cleaning agent, filtering system
System (including reverse osmosis and ultrafiltration system), water closet, yarn fabric, leather and leather production system, or be used therewith
System.
The amount for being commonly used for controlling the biocide combinations of the invention of microorganism growth is that 10ppm to 5,000ppm lives
Property composition.In some embodiments of the invention, the active component of composition is with least 20ppm, either at least 50ppm or
At least 100ppm, either at least 150ppm or at least 200ppm amount presence.In certain embodiments, the activity of composition
Composition is with no more than 2,000ppm, or no more than 1,000ppm, either no more than 500ppm or no more than 400ppm, or
Person is no more than 300ppm, either no more than 250ppm or no more than 200ppm, either no more than 100ppm or is no more than
50ppm amount is present.Concentration mentioned above is in terms of the fluid composition containing biocide combinations.
Present invention also contemplates that a kind of method, it is reduced by the way that required biocide combinations are incorporated in material, or
Suppress, or the microorganism growth in the above-mentioned use region of prevention, especially in in-can preservation application.
Example
Existed using Kull, F.C et al.《Applied microbiology (Applied Microbiology)》9:538-541(1961)
Described in method determine the present invention biocide combinations synergy.
Formula for calculating index of cooperation (SI) is
Qa/QA+Qb/QB=SI
Wherein
QA=compounds A concentration (ppm), individually work generation terminal (grow/not growing)
Qa=compounds A concentration (ppm), in form of mixtures, it produces terminal (grow/not growing)
QB=compounds B concentration (ppm), individually work generation terminal (grow/not growing)
Qb=compounds B concentration (ppm), in form of mixtures, it produces terminal (grow/not growing)
In this research, biocide terminal is defined as presenting the bacterium of at least 4 times logarithms in the case where specifying time of contact
Or yeast reduces or kept bacterium or the yeast counts of maximum 2 times of logarithms.If terminal can not be established, then that is tested kills livestock
The maximum concentration of agent will act as the terminal for calculating, and SI will with " be less than or<" value record.
When SI has the value less than 1, it was demonstrated that the synergy of two kinds of biocides.If SI is equal to 1, then mixture
Accumulative action is shown, and if SI is more than 1, then mixture shows antagonism.
The minimum inhibition test (MIC) of design can prevent bacterium, yeast or fungi in defined nutrient solution to assess
The least concentration of the biocide of growth, biocide admixture or biocide combinations.After cultivation, based on can visually examine
The turbidity of survey evaluates sample.
For biocide, this test is carried out in the case where dilution gfactor is 1.5.
Following biocide products/mixture is tested for two kinds of bacterium bacterial strains and a primary yeast：
MIC (MIC) testing scheme
1. test sample is prepared with same volume in transparent vessel.Biocide dilution is in Tryptic Soy nutrient solution
(TSB) under pH 7.3 (for bacterium) and in malt extract nutrient solution (MEB) under pH 5.4 (for fungi bacterium
Strain) carry out.
For every kind of biocide products and species, by being 1.5 in dilution gfactor in the case of carry out serial dilution come
16 samples are prepared in duplicate.
For every kind of microbial strains, two samples without any biocide of addition are used as tester.
2. each test sample is inoculated with to produce about 1 × 10 respectively with microbial suspension6CFU/ml is (in bacterial species
In the case of) and about 1 × 105CFU/ml (for fungal species) level.
Prepare microbial suspension：
Bacterial cultures：
The ATCC numberings 15442 of Pseudomonas aeruginosa (Pseudomonas aeruginosa) DSM numberings 939
The ATCC numberings 6538 of staphylococcus aureus (Staphylococcus aureus) DSM numberings 799
Culture preserves in glycerol stocks form at -80 DEG C in cryovial, thawed and be then scattered with 100 μ l
On TSA agar plates.After being cultivated 1 day at 30 DEG C, bacterial strain is collected together with buffer solution (pH 7.3).
Use the concentration of standard count plate technology evaluation cell.
For inoculum, it is diluted in buffer solution (pH 7.3).
Yeast culture：
The ATCC numberings 10231 of Candida albicans (Candida albicans) DSM numberings 1386
Culture preserves in glycerol stocks form at -80 DEG C in cryovial, thawed and be then scattered with 100 μ l
On MEA (m alt extract agar) petri diss (petri dishes).
Yeast strain disk is cultivated 1-2 days at 28 DEG C, is then collected together with buffer solution (pH 5.0).
Based on total count plate result, inoculum is prepared.
3. cultivate test sample：
2 days at 30 DEG C of bacterium
2 days at 28 DEG C of yeast
4. visually it is read out by grow/not growing evaluation.After cultivation, the growth of microorganism causes muddiness,
Clarification represents not grow.After cultivation, show that the least concentration not grown is considered as MIC value in nutrient solution.
The result for two kinds of biocides that synergy is presented in directed toward bacteria and yeast is presented in table 1-3.
The diamines of table 1. and DTBMA are directed to the biocidal efficacies and synergy of Pseudomonas aeruginosa DSM numberings 939
The diamines of table 2. and DTBMA are directed to the biocidal efficacies and synergy of staphylococcus aureus DSM numberings 799
The diamines of table 3. and DTBMA are directed to the biocidal efficacies and synergy of Candida albicans DSM numberings 1386
Claims (6)
1. a kind of Synergistic antimicrobial compositions, it is included：(a) diamines；Disulfide group -2,2'- pair-benzyl acid amides (b)；Its
Described in diamines and disulfide group -2,2'- it is double-the weight ratio of benzyl acid amides is 10:1 to 1:10.
2. a kind of Synergistic antimicrobial compositions, it is included：(a) diamines；Disulfide group -2,2'- pair-benzyl acid amides (b)；Its
Described in diamines and disulfide group -2,2'- it is double-the weight ratio of benzyl acid amides is 9:1 to 1:10.
3. a kind of method for suppressing the growth of aqueous medium microorganism or the microorganism growth of control aqueous medium, it is included to institute
State aqueous medium and add composition according to claim 1.
4. a kind of method for suppressing the growth of aqueous medium microorganism or the microorganism growth of control aqueous medium, it is included to institute
State aqueous medium and add composition according to claim 2.
5. a kind of aqueous medium, it includes Synergistic antimicrobial compositions according to claim 1.
6. a kind of aqueous medium, it includes Synergistic antimicrobial compositions according to claim 2.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562121943P | 2015-02-27 | 2015-02-27 | |
| US62/121943 | 2015-02-27 | ||
| PCT/US2016/018613 WO2016137830A1 (en) | 2015-02-27 | 2016-02-19 | Synergistic antimicrobial composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107205384A true CN107205384A (en) | 2017-09-26 |
| CN107205384B CN107205384B (en) | 2022-07-05 |
Family
ID=55442913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201680008326.6A Active CN107205384B (en) | 2015-02-27 | 2016-02-19 | Synergistic antimicrobial compositions |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20180042227A1 (en) |
| EP (1) | EP3261438B1 (en) |
| JP (2) | JP2018507845A (en) |
| CN (1) | CN107205384B (en) |
| BR (1) | BR112017016724B1 (en) |
| WO (1) | WO2016137830A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018005588A1 (en) * | 2016-06-30 | 2018-01-04 | Dow Global Technologies Llc | Synergistic combination of 3-iodo-2-propynyl-butylcarbamate and diamine |
| EP3802122B1 (en) | 2018-05-25 | 2023-08-16 | Cryovac, LLC | Method of making an antimicrobial multilayer film |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2354771A (en) * | 1999-10-01 | 2001-04-04 | Mcbride Ltd Robert | Bactericide combinations in detergents |
| WO2003062149A2 (en) * | 2002-01-22 | 2003-07-31 | Lonza Inc. | Antimicrobial composition including a triamine and a biocide |
| CN101453899A (en) * | 2006-05-26 | 2009-06-10 | 阿奇化工公司 | Isothiazolinone biocides enhanced by zinc ions |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8904844D0 (en) | 1989-03-03 | 1989-04-12 | Albright & Wilson | Biocidal compositions and treatments |
| BRPI0817718A2 (en) * | 2007-10-01 | 2015-10-13 | Basf Se | rondenticidal mixture, rodenticidal bait formulation, use of a rodenticidal bait formulation, method for combating rodent pests, and bait box |
| EP2671449A1 (en) | 2012-06-06 | 2013-12-11 | Construction Research & Technology GmbH | Use of vanadium pentoxide particles as a biocide |
| JP5995294B2 (en) * | 2012-06-29 | 2016-09-21 | ライオン株式会社 | Liquid softener composition |
| JP5961872B2 (en) * | 2013-03-22 | 2016-08-02 | ライオン株式会社 | Liquid softener composition |
-
2016
- 2016-02-19 JP JP2017541593A patent/JP2018507845A/en active Pending
- 2016-02-19 CN CN201680008326.6A patent/CN107205384B/en active Active
- 2016-02-19 EP EP16706754.5A patent/EP3261438B1/en active Active
- 2016-02-19 WO PCT/US2016/018613 patent/WO2016137830A1/en active Application Filing
- 2016-02-19 US US15/551,440 patent/US20180042227A1/en not_active Abandoned
- 2016-02-19 BR BR112017016724-7A patent/BR112017016724B1/en active IP Right Grant
-
2021
- 2021-02-05 JP JP2021017827A patent/JP7064030B2/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2354771A (en) * | 1999-10-01 | 2001-04-04 | Mcbride Ltd Robert | Bactericide combinations in detergents |
| WO2003062149A2 (en) * | 2002-01-22 | 2003-07-31 | Lonza Inc. | Antimicrobial composition including a triamine and a biocide |
| CN101453899A (en) * | 2006-05-26 | 2009-06-10 | 阿奇化工公司 | Isothiazolinone biocides enhanced by zinc ions |
Also Published As
| Publication number | Publication date |
|---|---|
| US20180042227A1 (en) | 2018-02-15 |
| JP7064030B2 (en) | 2022-05-09 |
| EP3261438B1 (en) | 2018-12-19 |
| EP3261438A1 (en) | 2018-01-03 |
| WO2016137830A1 (en) | 2016-09-01 |
| BR112017016724B1 (en) | 2022-09-20 |
| CN107205384B (en) | 2022-07-05 |
| JP2018507845A (en) | 2018-03-22 |
| BR112017016724A2 (en) | 2018-04-10 |
| JP2021073294A (en) | 2021-05-13 |
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